Vetiver and Derivatives

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Material Review

Woody Notes in Perfumery —


Vetiver and Derivatives. Part I
Botanical origin, production, composition and fragrance compounds
by Danute Pajaujis Anonis, Chemist Perfumer

V
etiver is an important woody note in perfumery. The word vetiver, vetyver in French, originated in
Tamil:* vettiveru = vetti, worthless + veru, useless.1 The Indian term for vetiver is Khus, and in
30 Indonesia is known as Akar Wangi.

Botanical origin: Vetiver, Vetiveria • α- and β-Vetivone (vetiverone): Java and


zizanioides Staph., is a grass growing wild, Réunion oils were found to contain 7.5 to 35.1
semi-wild or cultivated in many parts of percent of ketones, depending on the method
the world, including India, Haiti, Java, used. The odor of vetiver is due chiefly to ketonic
Réunion Islands, China and Indonesia. sesquiterpenes. Only two of them, listed above,
Mode of production, yield, type of have been isolated.
oil: Vetiver oil is obtained by distillation of
Vetiveria zizanioides roots. Steam distil- • Vetivenols (vetiverols): These alcohols were
lation is a more recent method used, and investigated by various researchers in the begin-
it gives a better yield of the oil. The yield ning of the 20th century, but the results were
of the dried vetiver Java roots is from 1.5 inconclusive. Only by the middle of the century
to 2 percent, and that of vetiver Haiti var- did it become apparent that at least 60 percent of
ies from 1 to 1.5 percent.2 A more recent these sesquiterpene alcohols occurring in vetiver
VOL. 29 MAY 2004

source gives the yield of air-dried vetiver Java oil seemed to consist of a mixture of primary
Java roots as 2 to 3 percent.3 alcohols in which a tricyclid alcohol predomi-
The following types of vetiver oil are nates, while bicyclic alcohols amounted only to 10
available commercially: percent.

•.. vetiver Java • Vetivenyl vetivenate: An ester that vetivenic


•.. vetiver Haiti acid forms with vetivenol and which readily hy-
•.. vetiver Réunion drolyzes.
•.. vetiver China
•.. vetiver Indonesian • Palmitic acid.
•.. vetiver redistilled
•.. vetiver de-ironized • Benzoic acid: In considerable amounts.
•.. vetiver resinoid
• Vetivene: A colorless and odorless sesquiterpene.
PERFUMER & FLAVORIST

Chemical Composition
The chemical composition of vetiver oil In 1976, a study of the carbonyls of Haitian vetiver
was studied in the beginning of the 20th oil was done. Seven novel sesquiterpenoid and norses-
century. Theulier studied the physico- quiterpenoid carbonyls were characterized. The major
chemical properties of fractionated vetiver isomer of dihydro β-vetivone had “a strong rich woody
oils distilled in France and on Réunion peppery odor,” while the remaining novel carbonyls
Island. Other investigations were carried were of a general woody type odor. The researchers
out by various researchers, among them believed that all of the carbonyls play a role in achieving
Semmler.4 In the 1950s, the following com- the complex woody odor of vetiver oil.6
ponents of vetiver oil were identified:5 Among vetiver oil components characterized in
the early 1970s were α- and β-vetivones, the nors-
A language spoken by members of the Dravidians, an
* esquiterpene khusimone and three biogenetically
ethnic group from southeastern India and Ceylon. derived C-12 ketones, which were deemed to be the
most interesting. Spiroketone and khusim- Using flashchromatography, two olfactory important
one appear to play an important role in the fractions were obtained: (1) medium polar (hydrocar-
reconstruction of vetiver oil. Therefore, bons, ethers and ketones), and (2) polar alcohols and
total new syntheses of these compounds α,β-unsaturated ketones. The combination of distilla-
were developed.7 tion and repeated FC yielded several new compounds.
In the study of vetiver oils of different In the medium polar fraction, one of the sesquiter-
geographical origins, other researchers re- pene hydrocarbons that never isolated before in veti-
ported 95 compounds in the hydrocarbon- ver oil was cis-eudesmadiene. Among other isolated
rich section, fractionated via distillation of ethers were α-agarofuran and 4,7-epoxy spirovetiva-
vetiver oil Haiti, and suggested that more 1,11(12)-diene.
than 150 components were present in the In the polar fraction, the transformation of second-
total vetiver oil.8 ary alcohols to methyl ethers; subsequent split tube
In 1977, a synthesis of β-vetivone via distillation gave 30 new sesquiterpene ethers after
base-catalyzed spiroannelation of pheno- repeated FC. Olfactory comparison of the odor of
lic tosylates was reported.9 A 1978 patent several methyl ethers and their corresponding alcohols
covered a new synthesis of khusimone.10 showed that the odor of the methyl ethers was more
6,6,7-Trimethyl-tricyclo [5.2.2.01,5] undec- earthy, khusimone-vetiver or patchouly-like, while the
32 8-en-2-one was given as the starting mate- alcohols had woody odor tonalities with amber, sweet
rial for this synthesis. This compound was and grapefruit undertones.12
described as having a woody, sandalwood-
like odor with vetiver nuances, thus being Synthetic Compounds
of interest. In 1989, another synthesis of Vetiver has a lasting woody odor with a hint of cam-
khusimone was reported, starting from phoraceous, earthy and musty undertones. It has
(S)-6,6-dimethyl-5-methoxycarbonylmethyl- points in common with violet-orris and patchouli type
2-cyclohexen-1-one. Overall yield was 6.9 odors, and it blends well with sandalwood and rose
percent.11 odors. Vetiver is especially effective with musky odors.
In 1996, an analysis of vetiver Haiti Several of the modifiers of vetiver odor are listed in T-1.
was reported that showed that the main
constituents were isovalencenol, β-vet- Vetiver Imitations
ivone and khusimol. Because vetiver was Because of the complexity of vetiver oil it is difficult
a very complex oil, it is a difficult task to to reproduce the vetiver odor. Several early imitations
separate and elucidate the structure of its were developed; some served in the past to fraud the
VOL. 29 MAY 2004

components. natural oil. Here are several examples:

Odor characteristics of tridecan-x-ones (x = 2,3,4,5 and 6) T-1


For lift and freshness To add To add Folial/green Spicy Woody Fixatives
floralcy sweetness
Aldehyde C-10 Aurantiol Coumarin Hexenyl acetate Isoeugenol Cedarwood Amyl salicylate
Aldehyde C-11 Jasmine Labdanum Methyl octine Sandalwood Benzophenone
resinoid carbonate
Aldehyde C-12 Lilial Musk ketone Phenylacetaldehyde Dimethyl
(MNA) dimethyl acetal hydroquinone
PERFUMER & FLAVORIST

Bergamot Nerol Styrax resinoid Diphenyl oxide


Cassie Neroli Tolu balsam Isobutyl
salicylate
Citraldimethyl acetal Rhodinol Vanilla resinoid Musks (various
types)
Clary sage Rose Vanillin
Geranonitrile Terpineol
Lavender Ylang ylang
Orange oil
Thyme
Ylang ylang
Complex of Vetiver Oil No. 113 sandalwood EI 70
vetiver oil 50.00 patchouli 10
sandalwood 40.50 cloves 35
copaiba balsam 8.00 jasmin synthetic 100
Rhodinol 0.50 rose synthetic 80
Exaltone 0.01 isobutyl salicylate 70
99.00 cinnamic alcohol 50
heliotropin 100
Vetiver Synthetic No. 2 coumarin 50
vetiver bourbon 225 tonka resinarome 20
cedarwood 150 aldehyde C-12 (MNA) 10% 15
copaiba balsam 100 1000
solvent 25
500 Cuir de Russie16
birch tar oil 60
Vetiver Synthetic No. 3 castoreum 10% 150
cedarwood 145.0 rose otto 20
sandalwood 135.0 styrax resinoid 100
guaiacwood 75.0 bergamot 100
hercolyn Atlas 70.0 sandalwood EI 10
34 vetiver Haiti
vetiver acetate
55.0
40.0
patchouli
jasmin absolute
5
50
labdanum resinoid 20.0 musk ambrette 50
aldehyde C-18 20.0 musk ketone 80
methyl ionone 15.0 Exaltolide 10% 20
tolu balsam 12.5 vetiver acetate 100
isobutyl quinoline 7.5 tonka resinoid 30
cade oil 10% 5.0 vanilla resinoid 20
600.0 vanillin 50
labdanum resinoid 100
clary sage 5
More recent vetiver specialties approxi-
oakmoss decolorized 10
mate the odor of vetiver oil, but leave much tuberose absolute 7
to be desired in regard to lastingness and acetophenone 3
fixative power. cassie absolute 10
lemon oil 20
1000
Traditional Fragrance Compounds
Let us take a look at a number of illus- Foin Coupé (New Mown Hay)17
VOL. 29 MAY 2004

trative fragrance compounds containing bergamot 90


vetiver or its derivatives. coumarin 120
jasmin absolute 100
rose absolute 20
Aldehydic Chypre14
cassie absolute 10
clary sage 35
oakmoss absolute 12
mousse de chene absolute 50
anisic aldehyde 18
nutmeg 35
linalool 20
patchouli 50
lavender 36
vetiver 95
clary sage 6
bergamot 125
vetiveryl acetate 24
orris concrete 25
hydroxycitronellal 20
orange oil 30
methyl anthranilate 6
sandalwood 90
civet infusion 3% 50
orange flower absolute 30
musk tonkin infusion 3% 200
jasmin absolute 30
ylang ylang 12
ionone 95
amyl salicylate 60
methylionone 90
isobutyl phenylacetate 30
PERFUMER & FLAVORIST

labdanum absolute 40
isobutyl benzoate 12
coumarin 25
tuberose absolute 20
heliotropin 90
mimosa absolute 18
vanillin 20
ionone a 20
musk ketone 50
methoxyacetophenone 30
aldehyde C-11 10% 75
aldehyde C-12 (MNA) 10% 6
aldehyde C-10 10% 75
sandalwood EI 60
aldehyde C-12 (MNA) 10% 50
1000
1205

Chypre I15 Traditional illustrative perfume compounds


mousse de chene 50 presented in this article were developed before
bergamot 225
dermatological consideration took effect. Therefore,
vetiver Bourbon 75
lavender 50 few components in these formulas would be acceptable
today unless a) used in limited percentages or b) spe-
cially processed. In the first case, relevant Austria (October 4-6, 1992).
materials include angelica, cinnamon,
7. G.H. Büchi, 7th Int. Congr. Ess. Oils, Scientific Section: Special
cinnamic alcohol, citrus oils and oakmoss, Lecture No. 4. p 87, Kyoto, Japan (October 7-11, 1977).
and in the second, bergamot and styrax
8. S. Lemberg and R.B. Hale, 7th Int. Congr. Ess. Oils, paper 117,
resinoid. Other components have been Kyoto, Japan (October 7-11, 1977).
completely eliminated, including musk
ambrette. We shall discuss this subject 9. S. Torii, K. Uneyama and K. Okamoto, ibid., paper 94.
matter in greater detail in the second part 10. G.H. Büchi and A. Hauser, US Patent 4,124,642, November 7,
of this article. 1978, assigned to Firmenich SA, Switzerland, cf Fragrances and
Flavors. Recent developments: Chemical Technology Review, No.
156, p 108-109, Edit. S. Torrey, Noyes Data Corp., Park Ridge,
Address correspondence to Danute Pajaujis Anonis, NJ (1980).
Chemist Perfumer, 98-41 64th Road, #6F, Rego Park,
NY 11374-3408. 11. K. Sakurai, T. Kithara and K. Mori, 11th Int. Congr. Ess. Oils, Fragr.
Flav., Proceedings: v 5, p 137-141, New Delhi, India (November
12-16, 1989).
References
12. D. Wolf, P. Weyerstahl and H. Marschall, Int. Symp. Ess. Oils,
1. The American Heritage Dictionary of the English Vienna, Austria (1996).
Language (Fourth Edition). Houghton Mifflin Co.,
36 Boston. 13. R. Cerbelaud, Formulaire de Parfumerie, p 313, Editións Opéra,
Paris (1951).
2. E. Guenther, The Essential Oils. Volume 4, p 161,
173, Van Nostrand Co., New York (1952). 14. R.M. Gattefossé, Formulaire de Parfumerie et de Cosmétologie,
p 197-198, Girardot & Cie, Paris (1950).
3. H.L. Tan, 7th Int. Congr. Ess. Oils, Kyoto, Japan
(October 7-11, 1977), General Session: Special 15. Ibid., p 82.
Lecture, p 50.
16. P. Jellinek, Das Praktikum des Modernen Parfuemeurs, p 68, Urban
4. Guenther, ibid., p 170. & Schwarzenberg, Wien (1949).

5. Ibid., p 170-171. 17. Ibid., p 65. ■

6. B.D. Mookherjee, R.W. Trenkle and R.A. Wilson,


12th Int. Congr. Ess. Oils, Fragr. Flav., Vienna,
VOL. 29 MAY 2004
PERFUMER & FLAVORIST
Material review
Woody Notes in Perfumery
Vetiver, derivatives and aroma chemicals. Part II

Danute Pajaujis Anonis, Chemist Perfumer A number of popular fragrances


contain vetiver or its derivatives,
including Chanel No. 5 (Chanel)

I
n the first part of this article (Perfumer & Flavorist, May 2004),* I discussed various vetiver types, the com-
position of vetiver oils of different origin, showed a few early vetiver imitations and illustrated a number of
traditional perfume compounds. In this article, I shall exemplify additional types of traditional perfume
46 compounds containing vetiver or its derivatives.

Traditional Fragrance Compounds 60 heliotropin


Fougerè No. 6 60 vetiver Réunion
140 geranium Bourbon 50 orris resinoid
100 vetiver 45 neroli synthetic
100 lavender 45 rose synthetic
50 amyl salicylate 1000
50 coumarin
40 cananga
Opoponax No. 3
VOL. 30 SEPTEMBER 2005

10 patchouly
200 bergamot
10 solvent
80 benzoin resinoid
500
50 vanillin
40 vetiver
Lavender Water1
32 coumarin
500 lavender oil French 35 musk ambrette
50 lavender absolute
25 lemon c.p.
150 bergamot
16 castoreum resinoid
30 musk Tonkin infusion 3%
8 patchouly
20 civet infusion 3%
486
10 neroli bigarade
20 orange flower absolute
20 petitgrain Grasse Origan Base No. 2903
30 orange oil sweet 200 Raldeine D Giv.
50 vetiveryl acetate 100 cassie synthetic No. 133
5 Tonka resinoid 100 vetiver Java
5 hydroxycitronellal 80 carnation synthetic No. 117
5 clary sage 45 rose synthetic No. 163
5 estragon oil 40 ylang Bourbon
PERFUMER & FLAVORIST

5 cloves 70 jasmin synthetic No. 51


10 styrax resinoid 97 amyl salicylate
20 benzoin resinoid 40 neroli synthetic No. 75
10 labdanum resinoid 20 rhodinol
30 vanilla extract 10% 40 opoponax resinoid
15 methylionone 23 musk ketone
1000 10 musk ambrette
10 coumarin
Mimosa No. 5412 50 heliotropin
300 ylang synthetic 65 vanillin
375 bergamot synthetic 6 patchouly
65 sandalwood E.I. 2 aldehyde C-12 (L)
*The heading of T-1 (p.32) was a printing error. It should
2 mousse de chêne absolute
be: “Modifiers of vetiver odor” 1000
Peau d’Espagne4 80 patchouly
4 birch tar oil rectified 30 sandalwood E.I.
45 castoreum infusion 5% 20 oakmoss resinoid 50%
270 civet absolute 10% 10 geraniol
55 sandalwood E.I. 20 musk ketone
70 bergamot 950
35 neroli bigarade
7 fleurs d’oranger absolute Dermatological Consideration
55 rose oil Bulgare Most of the illustrated traditional perfume
50 musk ambrette compounds were developed before the
35 musk ketone advent of dermatological considerations.
55 musk Tonkin Today, some components in these formulas
10 Tonka absolute would (1) be prohibited, (2) have to be
13 coumarin
2 patchouly
14 jasmin absolute
2 cassie absolute
45 tolu resinoid 47
25 styrax resinoid
20 ylang ylang oil
100 vetiverol
17 cloves
25 lemon c.p.
45 petitgrain Grasse
1000

Rose V5
phenyl ethyl alcohol 425 cm3
rhodinol 400 cm3
jasmin synthetic 50 cm3
nerol 25 cm3
vetiver 15 cm3
sandalwood 10 cm3
neroli oil 10 cm3
tuberose oil 10 cm3
rose oil 10 cm3

Vetiver Compound6
vetiver Java 140 g
vetiver Bourbon 200 g
sandalwood 100 g
hydroxycitronellal 120 g
cinnamic alcohol 60 g
jasmin synthetic 90 g
heliotropin 80 g
coumarin 50 g
musk ketone 50 g
musk ambrette 10 g

And a more recent vetiver


compound is:

Vetiver Bouquet for Men


400 vetiver Bourbon
150 cedryl acetate
120 methyl ionone
120 Grisambrol 10%
(Firmenich)
specially processed or (3) be limited in percentage vetiver, vetiver acetate-like
used, in accordance with IFRA’s (International Fra- • Khusimone (7,7-dimethyl-6-methylene
grance Association) recommendations. For example, tricyclo [6,2.1.01,5] undecan-2-one): has
use of musk ambrette is prohibited. been found to be mainly responsible for
the characteristic odor of vetiver8
In the second category are: • 2-Heptanol, 3,4,5,6,6-pentamethyl (Ko-
• Citral: can be used in conjunction with perfume hinool - IFF): woody, ambery, vetiver
materials preventing sensitization, such as pinene • Rootanol 100 (BASF): minty, earthy,
• Styrax: only vacuum distillation or extraction with reminiscent of vetiver roots
ethanol should be used • 2,5,10-Trimethyl 1,2,5,9-cyclododeca-
• Opoponax: only obtained by extraction of solvents trien-l-yl methyl ketone and isomers
or steam distillation (Trimofix - IFF): amber, woody note
with vetiver and tobacco nuances
In the third category are: • Vetynal extra (Givaudan): caryophyllene
• Bergamot: because of its phototoxicity, the level acetate main component, woody, used
in consumer products used on skin exposed to sun- as extender of vetiver notes
shine should not exceed 0.4 percent • Vethymine (2,4-diethoxy-5-methyl-
• Cinnamic alcohol: limited to 8 percent in con- pyrimidine): earthy, dusty, woody and 49
sumer products rooty with strong vetiver, patchouli and
• Hydroxycitronellal: limited to 5 percent in fra- agarwood nuances9
grance compounds • Vetyval, vetyvertone (4-cyclohexyl-2-
• Lemon oil c.p.: limited to 2 percent in consumer methyl-2-pentanone)10
products • Vetylbois (1,4 dimethoxy-2-terbutyl ben-
• Oakmoss absolute: limited to 0.6 percent in con- zene): woody with vetiver and patchouli
sumer products nuances11

If older fragrances have to be adapted to today’s


dermatological requirements, future fragrances are
facing even more stringent regulations.
Vetiver oil and derivatives
Meschede and Duclos described the changing
situations in current and future European legislation: are valuable perfume mate-
1. Essential oils and related products in Europe and
shipped to Europe will be facing new restrictions. rials used in many women’s
Apparently, the European Parliament will be making
most regulating decisions in Brussels. 2. The new leg- and men’s fragrances and
islation requires, among other things, the labeling of
26 substances alleged to be allergens identified by the
Scientific Committee for Cosmetics and Non-Food
in various cosmetic and
Products (SCCNFP) for all skin products. 3. The new
legislation requires among other things a labeling of
soap perfumes.
26 substances alleged to be allergens identified by the
Scientific Committee for Cosmetics and non-Food One patent covers isolongifolene es-
Products (SCCNFP) for all skin contact products. No ters.12 These esters “have valuable perfum-
differentiation as to the origin of these substances ery properties, particularly as replacements
(coming from essential oils or synthetics) was made. for vetiverol derivatives.”
The authors listed 59 essentials oils illustrating their The second patent describes a genus
total percentage of allergens from 0-90. Even veti- of substituted hexahydro acetonaphtones
ver oil would be a “culprit,” listed in the 0-5 percent having a structure containing a carbon-car-
category.7 bon double bond and carbon-carbon single
bonds, possessing multifaceted aromas of
Aroma Chemicals and Specialties sweet, woody, citrusy, vetiver-like, musky,
Let us take a look at different aroma chemicals with leathery, peppery, hay and green fragrance
woody vetiver and multifaceted odors: notes.13 They are useful fragrance ingre-
• Guaiyl acetate (guai-l(5)-en-ll-ol:acetate) (IFF): dients for perfumes, colognes, cosmetic
woody, vetiver, balsamic powders, soaps and detergents.
• Isobutylionone (Bedoukian): woody, vetiver An example of a hexahydro acetonaph-
• α-Isomethyl ionol (Bedoukian): woody, vetiver tone derivative used to impart a rich,
• Methyl cedryl ketone (Vertofix Coeur - IFF): green, woody note of vetiver is given:
woody, vetiver, leather with musky undertones Vetiver Fragrance
• Methyl tetrahydroionol acetate (Bedoukian): 10 labdanum resinoid
50 hexahydro acetonaphtone derivative background. The 24-h dry-out odor was strong,
25 cedrol warm, woody.
5 cedryl acetate
1 isobutyl quinoline Application
2 α-ionone Vetiver oil and derivatives are valuable perfume mate-
15 caryophyllene rials used in many women’s and men’s fragrances and
2 eugenol in various cosmetic and soap perfumes. Vetiver root
has been employed in the Orient since antiquity. The
The above fragrance compound may be dried root is used to scent clothes lines, by itself or in
used in a cologne at a concentration of 2.5 a form of sachet.
percent in 85 percent aqueous alcohol, and Vetiver and its derivatives are natural fixatives and
into a handkerchief perfume at a concen- are also modifiers of musky odors. Vetiverol is espe-
tration of 20 percent in 95 percent aque- cially suitable as a background note in floral bouquets.
ous alcohol. Used in a powder detergent Vetiver was used in old-fashioned violet pomade as
at a concentration of 0.7 percent, it will fixative.
produce a vetiver aroma with deep green Vetiver gives a covering power and persistence in
and woody notes.
talcum powder perfumes. Vetiver also finds applica-
50 A third patent describes cyclohexene-3-
tions in various types of potpourri, combined with
nitriles, which can be readily synthesized.14
spicy, floral, citrus or lavender notes. In addition, it is
These nitriles have a good stability in acid
a component of perfumes used to impart a pleasant
and basic conditions; they do not oxidize
scent to cigar boxes.
easily, can withstand higher temperatures,
and are suitable in soap, detergents and It is interesting to note that vetiver is considered an
personal care products. insect repellent, probably due to khusimone, a minor
In the preparation of mixed 3,5-di- but essential component of vetiver oil with insect
methyl- and 2,4-dimethyl-3-cyclohexene repellent power.
nitriles, the odor of combined fractions Here is an illustrative list of a number of earlier and
eight to 18 had a strong green, cuminic later fragrances containing vetiver or its derivatives:
VOL. 30 SEPTEMBER 2005

note with herbal, cinnamic and woody Arpège (Lanvin), Chanel No. 5 (Chanel), Femme (Ro-
PERFUMER & FLAVORIST
chas), Miss Dior (Dior), Shalimar (Guerlain), Cravache
(Piguet), L’O (Lancôme), Mystère de Rochas, Bales-
tra (ICR), Anais Anais (Cacherel), Silences (Jacomo),
Sheherazade (J. Deprez), Bois des Iles de Chanel
(1920s, reappeared in 1993), Paradox (Jacomo), Tiffany
(Tiffany & Co.), Paco Energy (Paco Rabanne), Must
(Cartier), Eau de Vetiver (Guerlain), L’Eau Cheap et
Chic (Moschino), Coriolan (Guerlain), Tiffany for Men
Sport Cologne, and the 2004 fragrance Le Baiser du
Dragon (Cartier).

Conclusion
Vetiver and its derivatives are likely to remain im-
portant woody note components in a broad spectrum
of men’s and women’s fragrances in the foreseeable
future. In spite of the pessimistic prognosis of G. and
F. Robert, who include vetiver oil among the vanish-
ing raw materials because of its popularity and huge
51
world consumption of natural products, vetiver oil
is still available and used in fragrances released in
2004.15 Vetiver will continue to remain an important
ingredient because it is difficult to replace/substitute.
The newer vetiver specialties approximate the initial
vetiver odor, but leave much to be desired in compari-
son to vetiver oil’s lasting fixative power.
Address correspondence to Danute Pajuajis Anonis, 98-41 64th Road,
Rego Park, NY 11374.

References

1. P. Jellinek, Pratikum des Modernen Parfuemeurs. Wien: Urban


& Schwarzenberg, p. 69 (1949).

2. O. Gerhardt, Das Komponieren in der Parfuemerie. Leipzig:


Akademische Verlagsgesellschaft MBH, p. 279 (1931).

3. Ibid., p.180

4. Jellinek, p.76

5. Fouquet, La Technique Moderne et les Formules de la Parfumerie.


Paris et Liège: Ch Béranger, p. 124 (1951).

6. R.M. Gattefossé, Formulaire de Parfumerie et de Cosmétologie.


Paris: Girardot & Cie, p. 83 (1950).

7. F.P. Meschede and T. Duclos, Perfumer & Flavorist, 1(28), 48-53


(2003).

8. G.H. Büchi and A. Hauser, U.S. Patent 4,124,642. November 7, 1978;


assigned to Firmenich, SA, Switzerland, cf. Fragrances and Flovors.
Recent Developments. Chemical Technology Review No. 156. Edit.,
S. Torrey, Noyes Data Corporation, Park Ridge, NJ, p. 108 (1980).

9. A. Boix Camps, Perfum. Flavor., 1(24), 20 (1999).

10. Ibid., p. 24

11. Ibid., p. 26

12. U.S. 3,647,847 (assignee: Bush Boake Allen Limited, London,


England); Cosmetics and Perfumery, 1(89), 60 (1974).

13. W.L. Schreiber, J.N. Siano and E.J. Shuster, U.S. Patents: 4,076,749;
Feb. 28, 1979; 4,107,066; Aug. 15, 1978; 4,108,799; Aug. 22, 1978 and
4,156,695; May 29, 1979; all assigned to International Flavors and
Fragrances, Inc., cf Fragrances and Flavors. Recent Developments.
Chemical Technology Review, ibid., pp. 110-114.

14. R.S. De Simone, U.S. Patent 4,146,507; March 27, 1979; assigned
to Polak’s Frutal Works.

15. G. Robert and R. Robert, Perfum. Flavor., 4(29), 34 (2004). ■

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